Azoliums and Ag(I)‐N‐Heterocyclic Carbene Thioglycosides: Synthesis, Reactivity and Bioactivity

Dmytro Ryzhakov (1) , Audrey Beillard (2) , Franck Le Bideau (1) , Riyadh Ahmed Atto Al‐shuaeeb (1) , Mouad Alami (1) , Xavier Bantreil (2) , Aurore Bonnemoy (3) , Arnaud Gautier (3) , Frédéric Lamaty (2) , Samir Messaoudi (1)

1 BioCIS - Biomolécules : Conception, Isolement, Synthèse
2 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
3 ICCF - Institut de Chimie de Clermont-Ferrand

A versatile protocol for the synthesis of azolium thioglycosides is reported. This protocol is based on a PdG3-catalyzed Migita cross-coupling between p-di-iodo azoliums and protected or unprotected β-1-thioglucose partners. Moreover, a solvent-free mechanochemistry approach was developed as a unique access to the corresponding Ag(I)-N-heterocyclic carbene thioglycosides. Finally, chemical reactivity and antiproliferative bioactivity were examined with azoliums and Ag(I)-NHC thioglycosides. This study demonstrates a promising potential of these newly synthesized carbohydrate-based N-heterocyclic derivatives.

Domaines: Chimie organique; Chimie thérapeutique

Dmytro Ryzhakov, Audrey Beillard, Franck Le Bideau, Riyadh Ahmed Atto Al‐shuaeeb, Mouad Alami, et al.. Azoliums and Ag(I)‐N‐Heterocyclic Carbene Thioglycosides: Synthesis, Reactivity and Bioactivity. European Journal of Organic Chemistry, 2022, 2022 (9), pp.e202101499. ⟨10.1002/ejoc.202101499⟩. ⟨hal-03648181v2⟩